Dichloromethane → HCID 66738318, compound

HRID 2047063Notes

Reaction equation

HRID 2047063 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3](B(O)O)[CH:2]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(Cl)Cl.[CH3:25][Si:26]([CH3:63])([CH3:62])[CH2:27][CH2:28][O:29][CH2:30][N:31]([CH2:54][O:55][CH2:56][CH2:57][Si:58]([CH3:61])([CH3:60])[CH3:59])[C:32]1[N:37]2[N:38]=[CH:39][C:40](I)=[C:36]2[N:35]=[C:34]([CH:42]2[CH2:47][CH2:46][CH:45]([CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])[CH2:44][CH2:43]2)[CH:33]=1>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:61][Si:58]([CH3:59])([CH3:60])[CH2:57][CH2:56][O:55][CH2:54][N:31]([CH2:30][O:29][CH2:28][CH2:27][Si:26]([CH3:63])([CH3:62])[CH3:25])[C:32]1[N:37]2[N:38]=[CH:39][C:40]([C:3]3[CH:2]=[N:1][C:10]4[C:5]([CH:4]=3)=[CH:6][CH:7]=[CH:8][CH:9]=4)=[C:36]2[N:35]=[C:34]([CH:42]2[CH2:47][CH2:46][CH:45]([CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])[CH2:44][CH2:43]2)[CH:33]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 2734663Quinoline-3-boronic acidHCID 66733407HCID 66733407, compound

Product 1

HCID 66738318HCID 66738318, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a 40 mL scintillation vial was charged 3-quinoline boronic acid (0.73 mmol, 127 mg), K3PO4 (1.46 mmol, 310 mg) and PdCl2(dppf).CH2Cl2 (0.049 mmol, 40 mg). To this mixture was added a solution of ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate (335 mg, 0.49 mmol) in dioxane (9 mL). To this suspension was added distilled H2O (1 mL). The resulting solution was stirred at 100° C. for 18 hours. The reaction was concentrated in vacuo and then purified via silica gel chromatography (0% to 60% ethyl acetate in hexanes gradient) to yield ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetate (198 mg, 287 μmol, 59% yield) as yellow oil.

Workup

  1. additionTo this suspension was added
  2. distillationdistilled H2O (1 mL)
  3. concentrationThe reaction was concentrated in vacuo
  4. custompurified via silica gel chromatography (0% to 60% ethyl acetate in hexanes gradient)

Sources & evidence

ORD record
ord-093d2aa620f54a7dbb13e62ac5d239fc
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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